Application of BF3•OEt2 in Organic Synthesis as a Catalyst or Synthon

doi:10.6023/cjoc202303006

Abstract

BF₃•OEt₂, as a typical Lewis acid catalyst with excellent catalytic capacity, plays an important role in many reactions, such as coupling, cyclization and rearrangement, and it is widely used in the synthesis of natural products, pharmaceutical molecules and other functional molecules. Interestingly, in the presence of water, BF₃•OEt₂ can be combined with water to form Bronsted acid, which can also promote the coupling, addition, and other reactions. At the same time, BF₃•OEt₂ is not only limited to be a catalyst, but also can be used as a synthon to mildly construct compounds containing B, F and BF₂ structure molecules, which plays an important role in the field of catalytic ligand and fluorescence molecules. Based on various catalytic reaction types using BF₃•OEt₂ and its different applications as a synthon, the research progress on the application of BF₃•OEt₂ in organic synthesis in recent years is reviewed. Looking forward to the future, with the in-depth study of BF₃•OEt₂, there will be more understanding of its performance and application, it is possible to develop more surprising catalytic systems and synthetic applications.

Key words: BF₃•OEt₂, Lewis acid, coupling reaction, addition reaction, boron difluoride compound

Cite this article

Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.

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Fig. & Tab. 7

Scheme 1. BF3?OEt2-catalyzed dealkoxy coupling

Scheme 2. Selective coupling of polyphenols to indole derivatives

Scheme 3. BF3?OEt2-catalyzed process of α-amino acetals with alkynes to pyrrole derivatives

Scheme 4. BF3?OEt2-catalyzed process to form seven-membered ring

Scheme 5. BF3?OEt2-catalyzed rearrangement of glycidol acetal

Scheme 6. Coupling reaction catalyzed by Br?nsted acid from BF3?OEt2 in the presence of water

Scheme 7. Dual application of BF3?OEt2 used as both catalyst and synthon

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BF₃•OEt₂作为催化剂与合成子在有机合成中的应用进展

Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon

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BF3•OEt2作为催化剂与合成子在有机合成中的应用进展